About Plenful

Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Notable Capital, Bessemer Venture Partners, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI automation platform that healthcare teams rely on to operate smarter, faster, and more efficiently. Our technology empowers healthcare operators across hospital and health systems, pharmacies and payors to eliminate manual work, reduce administrative burden, and improve compliance, all while unlocking critical revenue to fund programs for their in-need patient populations.

Built by healthcare operators for healthcare operators, Plenful is driven by a deep understanding of the challenges facing today’s care teams. We’re passionate about equipping healthcare workers with world-class tools that deliver real, measurable impact, and we’re proud to serve 100+ leading health systems, pharmacies, and healthcare organizations across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Apply now to join our growing team.

About the Role

Plenful is hiring a Senior DevOps Engineer to join our engineering team and help build and scale the infrastructure, tooling, and deployment systems that power our product and engineering velocity. You'll work across our distributed workflow engine, serverless pipelines, containerized services, and Postgres-based data layer.

This role reports into engineering leadership and plays a key part in shaping how we build, deploy, and operate our platform as we grow. You'll focus on systems and workflows that let engineers move quickly and safely, while keeping our platform reliable, observable, and efficient.

You'll bring strong technical judgment, a pragmatic approach to automation, and a focus on reducing friction for other engineers. You'll work closely with backend and ML teams and help build a culture where infrastructure, reliability, and developer experience are clear, repeatable, and shared across the team. This role is hybrid.

What You’ll Do

Infrastructure, Platform, and Deployment

Design, build, and evolve our cloud infrastructure using infrastructure-as-code, focused on scalability, consistency, and ease of use.
Build and maintain CI/CD pipelines for fast, safe, repeatable deployments.
Standardize deployment patterns across serverless workloads, containerized services, and workflow orchestration systems.
Improve how services get provisioned, configured, and deployed so engineers can move fast without adding risk.

Developer Experience and Enablement

Build internal tooling and automation that simplifies common workflows for backend and ML teams.
Improve local and staging environments to cut friction in development and testing.
Let engineers self-serve infrastructure through well-designed abstractions, templates, and documentation.
Find and eliminate bottlenecks in the development and deployment lifecycle.

Observability, Reliability, and Performance

Define and evolve observability standards across metrics, logs, and tracing, focused on actionable insight.
Build systems that catch reliability risks, latency regressions, and performance issues before they become problems.
Partner with engineering teams to investigate and resolve performance bottlenecks across distributed systems, including serverless execution, containers, and Postgres.
Support incident response and root cause analysis, focused on preventing recurrence through better systems and automation.

Security, Compliance, and Operational Excellence

Automate security and compliance workflows: patching, access controls, audit readiness, and vulnerability management.
Build security and compliance practices into infrastructure and deployment pipelines.
Take part in the on-call rotation and respond to production issues, focused on restoring service and improving systems over time.
Contribute to blameless postmortems and make sure learnings show up in tooling, process, and documentation.

You May Be a Fit If

You have a bachelor's degree in Computer Science or a related field.
You've spent 7+ years in professional engineering at a B2B SaaS company.
You've built and operated production systems in cloud environments, ideally AWS.
You have hands-on experience with infrastructure as code (Terraform or similar), CI/CD systems, and modern deployment workflows.
You've worked with serverless compute patterns, containerized services, distributed workflows, and Postgres.
You understand observability tooling, performance debugging, and system behavior under load.
You can write scripts or services to automate infrastructure and developer workflows.
You have a high ownership mindset, empathy for teammates, straightforward communication, and a one-team attitude.
You're comfortable in a fast-paced startup environment with a bias for action and thoughtful engineering judgment.

Why You'll Love Working Here

🚀 Mission-Driven, World-Class Team — Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact
📈 Opportunities for Growth — Strengthen your expertise through collaboration with experienced, high-performing leaders across the organization
🏢 Flexible Hybrid Work Environment — We're remote-first, with meaningful office presence in San Francisco and New York. R&D roles follow a hybrid model, with two days per week in our San Francisco office

Benefits & Perks

🏥 Healthcare Coverage — Full medical, dental, and vision insurance for you and participation for your family
💰 401(k) with Company Match — Plenful matches 50% of your first 3% contributed
📊 Equity — Every full-time employee shares in our success
🌴 Unlimited PTO — Take the time you need, when you need it
🍽️ Daily Lunch Stipend — $100/week to cover your midday meals
💪 Wellness Stipend — $100/month to support your health and well-being
🚇 Commuter Benefits — $100/month for SF and NYC-based employees
👶 Parental Leave — Paid leave to support growing families